Open AccessA Tutorial on Selectivity Determination in C(sp2)–H Oxidative Addition of Arenes by Transition Metal Complexes
Author(s) -
Tyler P. Pabst,
Paul J. Chirik
Publication year - 2021
Publication title -
organometallics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.231
H-Index - 172
eISSN - 1520-6041
pISSN - 0276-7333
DOI - 10.1021/acs.organomet.1c00030
Subject(s) - chemistry , chemoselectivity , regioselectivity , oxidative addition , selectivity , transition metal , oxidative phosphorylation , aryl , transition state , chelation , halide , medicinal chemistry , reductive elimination , computational chemistry , photochemistry , stereochemistry , inorganic chemistry , organic chemistry , catalysis , alkyl , biochemistry
A Tutorial on factors that determine the selectivity in C(sp 2 )-H activation and functionalization reactions involving two-electron oxidative addition processes with transition metals is presented. The interplay of the thermodynamics of C(sp 2 )-H oxidative addition and kinetic influences upon regioselectivity are presented alongside pedagogically valuable experimental and computational results from the literature. Mechanisms and energetics of chelate-assisted C(sp 2 )-H oxidative addition are examined, as are concepts related to chemoselectivity in the oxidative addition of C(sp 2 )-H or C(sp 2 )-X (X = F, Cl, Br, I) bonds with aryl halide substrates.